WO2024219467A1 - ウイルス感染阻止剤、樹脂組成物及び合成樹脂成形体 - Google Patents
ウイルス感染阻止剤、樹脂組成物及び合成樹脂成形体 Download PDFInfo
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- WO2024219467A1 WO2024219467A1 PCT/JP2024/015429 JP2024015429W WO2024219467A1 WO 2024219467 A1 WO2024219467 A1 WO 2024219467A1 JP 2024015429 W JP2024015429 W JP 2024015429W WO 2024219467 A1 WO2024219467 A1 WO 2024219467A1
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- viral infection
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
Definitions
- the present invention relates to a virus infection inhibitor, a resin composition, and a synthetic resin molded product.
- Patent Document 1 proposes an antiviral article having a cured layer, the cured layer containing a cured product of a curable resin composition, an antiviral agent in which a carrier carries or contains silver ions, and an antioxidant, the antioxidant containing a phosphorus-based antioxidant.
- Patent Document 2 proposes an antiviral composition containing diiodomethyl-p-tolylsulfone and/or 3-iodo-2-propynyl butylcarbamate and polyhexamethyleneguanidine.
- the present invention provides a novel virus infection inhibitor that has excellent virus infection inhibitory effects.
- the viral infection inhibitor of the present invention includes a viral infection inhibitor compound having two secondary cyclic amino structures in the molecule.
- the resin composition of the present invention is characterized by containing a synthetic resin and the above-mentioned virus infection inhibitor contained in the synthetic resin.
- the synthetic resin molded article of the present invention includes a molded body containing a synthetic resin and the above-mentioned virus infection inhibitor contained in the molded body.
- the viral infection inhibitor of the present invention has a viral infection inhibitory effect against various viruses due to the action of the viral infection inhibitor compound, and exerts an excellent viral infection inhibitory effect against both enveloped and non-enveloped viruses.
- the viral infection inhibitor of the present invention contains a viral infection inhibitor compound having two secondary cyclic amino structures in the molecule as an active ingredient.
- the viral infection inhibitor exerts an excellent viral infection inhibitory effect due to the two secondary cyclic amino structures contained in the viral infection inhibitor compound.
- the content of the viral infection inhibitor compound in the viral infection inhibitor is preferably 50% by mass or more, more preferably 60% by mass or more, more preferably 70% by mass or more, more preferably 80% by mass or more, more preferably 90% by mass or more, more preferably 95% by mass or more, more preferably 99% by mass or more, and more preferably 100% by mass.
- the viral infection-inhibiting compound has two secondary cyclic amino structures in the molecule.
- a secondary cyclic amino structure is a structure in which the atoms constituting the compound form a ring structure, and this ring structure contains a secondary amino group.
- the secondary amino group refers to a divalent substituent (-NH-) generated by removing one hydrogen atom from an amino group (-NH 2 ).
- the "-" in -NH- and -NH 2 is a bond and means a single bond.
- a secondary cyclic amino structure refers to a structure in which the atoms constituting the compound form a ring structure, the atoms constituting this ring structure include a nitrogen atom, two bonds of this nitrogen atom are bonded to other atoms constituting the ring structure, and the remaining bond of the nitrogen atom is bonded to a hydrogen atom.
- the mechanism of the viral infection inhibitor's viral infection inhibitory effect is unknown, but is presumed to be as follows.
- the viral infection inhibitor compound has two secondary cyclic amino structures in its molecule, and is therefore capable of effectively interacting with viruses at the secondary cyclic amino structure portion, and it is believed that the viral infection inhibitor exerts an excellent viral infection inhibitory effect against both enveloped and non-enveloped viruses.
- the viral infection inhibiting compound has only one secondary cyclic amino structure, the interaction between the viral infection inhibiting compound and the virus is insufficient, and it is believed that the viral infection inhibiting effect of the viral infection inhibiting agent, particularly against non-enveloped viruses, is reduced. If the viral infection inhibiting compound has three or more secondary cyclic amino structures, the bulkiness of the secondary cyclic amino structures causes mutual interference, and it is believed that the interaction between the viral infection inhibiting compound and the virus is insufficient, and it is believed that the viral infection inhibiting effect of the viral infection inhibiting agent, particularly against non-enveloped viruses, is reduced. If the viral infection inhibiting compound has only a tertiary cyclic amino structure in the molecule, it is believed that the viral infection inhibiting effect, particularly against non-enveloped viruses, is insufficient.
- the secondary cyclic amino structure is an alicyclic structure in which multiple carbon atoms and one nitrogen atom are bonded in a ring, and a ring structure containing a secondary amino group in the alicyclic structure is preferred, a five-membered alicyclic structure in which four carbon atoms and one nitrogen atom are bonded in a ring, and a ring structure containing a secondary amino group in the alicyclic structure is more preferred, and a six-membered alicyclic structure in which five carbon atoms and one nitrogen atom are bonded in a ring, and a ring structure containing a secondary amino group in the alicyclic structure is more preferred, and a six-membered alicyclic structure in which five carbon atoms and one nitrogen atom are bonded in a ring, and a ring structure containing a secondary amino group in the alicyclic structure is more preferred.
- the secondary cyclic amino structure preferably does not contain an aromatic ring.
- aromatic rings also include fused aromatic rings formed by condensing monocyclic aromatic rings. Examples of aromatic rings include benzene rings, naphthalene rings, anthracene rings, biphenyl, and phenoxyphenyl.
- the aromatic ring is formed by removing one or more hydrogen atoms from either the aromatic ring or the fused aromatic ring, and is bonded to other atoms by a covalent bond.
- the viral infection inhibiting compound it is preferable that at least one of the two secondary cyclic amino structures is a tetramethylpiperidyl group having the structure shown in formula (1). In the viral infection inhibiting compound, it is more preferable that both of the two secondary cyclic amino structures are tetramethylpiperidyl groups shown in formula (1).
- the secondary cyclic amino structure is a tetramethylpiperidyl group shown in formula (1), the viral infection inhibiting agent exhibits excellent viral infection inhibiting effects against both enveloped and non-enveloped viruses.
- *1 is a bond and means a single bond.
- the secondary cyclic amino structure may form a salt.
- the salt of the secondary cyclic amino structure is not particularly limited, but an acid addition salt is preferred.
- acids for the acid addition salt include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, phosphorous acid, hydrobromic acid, maleic acid, malic acid, ascorbic acid, tartaric acid, lauric acid, stearic acid, palmitic acid, oleic acid, myristic acid, lauryl sulfuric acid, linoleic acid, and fumaric acid, and hydrochloride is preferred.
- the secondary cyclic amino structure is preferably directly bonded to the oxygen atom [oxygen atom bonded to the carbon atom of the keto group (-CO-)] constituting the ester bond [formula (3)], and it is more preferable that each of the two secondary cyclic amino structures is directly bonded to the oxygen atom constituting the ester bond.
- the viral infection inhibitor exhibits excellent viral infection inhibitory effects against both enveloped and non-enveloped viruses.
- *2 and *3 are bonds and represent single bonds.
- the viral infection-inhibiting compound preferably has a structure represented by formula (2), where n is a natural number.
- n is a natural number, preferably 2 or more, and more preferably 4 or more. n is preferably 14 or less, and more preferably 12 or less. When n is within the above range, the viral infection inhibitor exhibits excellent viral infection inhibitory effects against both enveloped and non-enveloped viruses.
- the molecular weight of the viral infection inhibiting compound is preferably 100 or more, more preferably 250 or more, and more preferably 400 or more.
- the molecular weight of the viral infection inhibiting compound is preferably 9000 or less, more preferably 7000 or less, more preferably 5000 or less, more preferably 1000 or less, more preferably 750 or less, and more preferably 500 or less.
- the molecular weight of the viral infection inhibiting compound is 100 or more, the viral infection inhibiting compound has a molecular structure that easily interacts with viruses, and exhibits a good viral infection inhibiting effect.
- the molecular weight of the viral infection inhibiting compound is 1000 or less, the compatibility of the viral infection inhibiting compound with the synthetic resin is improved, the dispersibility of the viral infection inhibiting compound in the synthetic resin is improved, and an excellent viral infection inhibiting effect can be imparted to the synthetic resin.
- the molecular weight of the viral infection inhibiting compound is the weight average molecular weight of the viral infection inhibiting compound.
- the weight-average molecular weight of the viral infection-inhibiting compound is a polystyrene-equivalent value measured by GPC (gel permeation chromatography).
- the measurement can be performed using the following measurement device and under the following measurement conditions.
- Gel permeation chromatograph Waters Corporation, product name "2690Separations Model” Column: Showa Denko Co., Ltd., product name "GPCKF-806L”
- Detector differential refractometer Sample flow rate: 1 mL/min Column temperature: 40°C Eluent: THF
- the viral infection inhibitory effect refers to the effect of eliminating or reducing the infectivity of the virus to cells, or preventing the virus from multiplying within the cells even if it infects.
- Methods for confirming the infectivity of such viruses include, for example, ISO 18184 and JIS L1922 for textile products, and ISO 21702 for plastics and non-porous surface products other than textile products.
- Other methods include the plaque method and hemagglutination unit (HAU) measurement method described in "Medical and Pharmaceutical Virology" (first published in April 1990).
- HAU hemagglutination unit
- the viral infection inhibitor effect of the viral infection inhibitor can be measured, for example, as follows.
- a viral infection inhibitor containing 5 parts by mass of a viral infection inhibitor compound is mixed with 95 parts by mass of an ultraviolet-curing acrylic paint to prepare a viral infection inhibitor paint.
- the viral infection inhibitor paint is applied to a polyethylene film with a wire bar coater #8 to a thickness of 18 ⁇ m to form a coating layer.
- the coating layer is irradiated with ultraviolet light having a wavelength of 365 nm at 25° C. so as to achieve an integrated light intensity of 500 mJ/cm 2 to cure the ultraviolet curable acrylic coating material, thereby forming a coating film having a thickness of 18 ⁇ m.
- a test specimen is prepared by cutting out a flat square piece of coating film with each side measuring 5.0 cm.
- the surface of the coating film on the obtained test specimen is wiped with a flat square piece of nonwoven fabric with each side measuring 10 cm by moving the nonwoven fabric back and forth 10 times to obtain the test coating film.
- the obtained test coating film is subjected to an antiviral test in accordance with ISO 21702.
- the virus infectivity (common logarithm value) (PFU/cm 2 ) of the test coating film is calculated by the plaque method.
- a blank coating film is prepared in the same manner as above, except that no viral infection inhibitor is added, and the viral infectivity (common logarithm value) (PFU/cm 2 ) is calculated based on this blank coating film in the same manner as above.
- the antiviral activity value is calculated by subtracting the viral infectivity value of the test coating from the viral infectivity value of the blank coating.
- a virus infection inhibitor containing 5 parts by mass of a virus infection inhibitor compound is melt-kneaded and mixed with 93 to 95 parts by mass of a synthetic resin to produce a resin composition, which is then press-molded to produce a sheet-like synthetic resin molded body with an average thickness of 1 mm.
- the surface of the obtained synthetic resin molded body is wiped with a flat square nonwoven fabric measuring 10 cm on a side by moving the nonwoven fabric back and forth 10 times, and this synthetic resin molded body is used as a test body.
- a blank reference body is prepared in the same manner as above, except that it does not contain the virus infection inhibitor.
- the antiviral activity value may be calculated in the same manner as above using the test body and blank reference body instead of the test coating and blank coating.
- the antiviral activity value 10 minutes after the start of the reaction in an antiviral test in accordance with ISO 21702 is preferably 2.0 or more, more preferably 2.5 or more, and even more preferably 2.8 or more. Regardless of the type of virus being evaluated, it is preferable that the antiviral activity value be 2.0 or more for at least one type of virus.
- the nitrogen atom content of the viral infection inhibiting compound is preferably 0.1% or more, and more preferably 0.5% or more.
- the nitrogen atom content of the viral infection inhibiting compound is preferably 20% or less, more preferably 15% or less, more preferably 10% or less, more preferably 8% or less, and more preferably 7% or less.
- the nitrogen atom content of the viral infection inhibiting compound is within the above range, the viral infection inhibitor exhibits excellent viral infection inhibiting effects against both enveloped and non-enveloped viruses.
- the nitrogen atom content of a viral infection-inhibiting compound refers to the percentage of the amount of nitrogen atoms relative to the total amount of atoms constituting the viral infection-inhibiting compound.
- Nitrogen atom content (%) of viral infection-blocking compound 100 x (total amount of nitrogen atoms contained in the viral infection-inhibiting compound) /Total atomic weight of virus infection-blocking compound
- the pH of a 5% by mass aqueous solution of the viral infection inhibiting compound at 25°C is preferably 8 or higher.
- the pH of a 5% by mass aqueous solution of the viral infection inhibiting compound at 25°C refers to the pH value at 25°C of a mixture obtained by adding 5 g of the viral infection inhibiting compound to 95 g of purified water and mixing uniformly.
- the mixture may be one in which the entire amount of the viral infection inhibiting compound is dissolved in purified water, or one in which the viral infection inhibiting compound is dissolved in purified water to form a saturated aqueous solution.
- the pKa1 of the viral infection inhibiting compound at 25°C is preferably 8 or more, more preferably 8.5 or more.
- the surface of the viral infection inhibiting compound is in an appropriate charge state in the interaction between the viral infection inhibiting compound and the virus, the virus is effectively captured, and the viral infection inhibiting effect of the viral infection inhibitor is improved.
- the pKa1 of the viral infection inhibiting compound at 25°C is preferably 12 or less, more preferably 11 or less.
- the acid dissociation constant Ka is defined by formula (b)
- the pKa is defined by the common logarithm (c) of the reciprocal of the acid dissociation constant Ka.
- pKa1 is defined as the acid dissociation constant of the conjugate acid of the viral infection inhibitory compound.
- the viral infection inhibitory compound is a polyamine, and the conjugate acid of the polyamine undergoes multiple ionization steps, but pKa1 refers to the pKa calculated based on the ionization constant of the first step.
- the pKa1 of a viral infection inhibiting compound at 25°C is a value measured by titration. Specifically, pKa1 can be determined by titrating the viral infection inhibiting compound with hydrochloride and sodium hydroxide at 25°C and measuring the pH at 25°C at the half-equivalent point (the point at which half the amount required for complete neutralization is dropped). If the secondary amino group of the viral infection inhibiting compound is in a free form, it can be converted to a hydrochloride and then the pKa1 can be determined by the above-mentioned method.
- a method for converting a free secondary amino group to a hydrochloride can be, for example, mixing the viral infection inhibiting compound with a 1 mol% aqueous hydrochloric acid solution, converting all of the secondary amino groups contained in the viral infection inhibiting compound to hydrochloride, and then removing the hydrochloric acid and water by a general method such as freeze-drying.
- the melting point of the viral infection inhibiting compound is preferably 40°C or higher, more preferably 60°C or higher, and even more preferably 80°C or higher.
- the melting point of the viral infection inhibiting compound is preferably 110°C or lower, and even more preferably 100°C or lower. If the melting point of the viral infection inhibiting compound is 40°C or higher, the temperature range in which the viral infection inhibiting compound can exist as a solid is expanded, improving the processability of the viral infection inhibitor. If the melting point of the viral infection inhibiting compound is 110°C or lower, the viral infection inhibitor is melted and mixed uniformly when kneaded with the synthetic resin, and an excellent viral infection inhibiting effect can be imparted to the synthetic resin.
- the melting point of the viral infection inhibiting compound refers to the temperature measured by differential scanning calorimetry in accordance with JIS K7121:1987.
- the virus infection inhibitor containing the virus infection inhibitor compound can be used by being contained in a base material as described below.
- the virus infection inhibitor containing the virus infection inhibitor compound can be uniformly dispersed in a synthetic resin, and can impart an excellent virus infection inhibitory effect to the synthetic resin. Therefore, it is preferable that the virus infection inhibitor is formed in a particulate form.
- the D90 particle size of the virus infection inhibitor compound is preferably 1 ⁇ m or more, more preferably 2 ⁇ m or more, preferably 2.5 ⁇ m or more, more preferably 3 ⁇ m or more, and more preferably 3.5 ⁇ m or more.
- the D90 particle size of the virus infection inhibitor compound is preferably 50 ⁇ m or less, more preferably 25 ⁇ m or less, preferably 22 ⁇ m or less, more preferably 20 ⁇ m or less, more preferably 18 ⁇ m or less, more preferably 16 ⁇ m or less, more preferably 14 ⁇ m or less, and more preferably 12 ⁇ m or less. If the D90 particle size is 1 ⁇ m or more, the surface area of the entire viral infection inhibiting compound is small, the agglomeration of the viral infection inhibiting agent is reduced, and the viral infection inhibiting compound and the virus are in a form that is easy to interact with each other, improving the viral infection inhibiting effect of the viral infection inhibiting product. If the D90 particle size is 50 ⁇ m or less, agglomeration of the viral infection inhibiting agent is prevented and the surface area is increased to facilitate contact with the virus, improving the viral infection inhibiting effect of the viral infection inhibiting product.
- the D90 particle size of a viral infection inhibiting compound is the particle size (90% cumulative particle size) at which the cumulative frequency (accumulation from particles with smaller particle sizes) in the volume-based particle size distribution measured by the laser scattering method is 90%.
- the D90 particle size of the viral infection inhibiting compound is the value measured based on the entire viral infection inhibiting compound.
- the viral infection inhibitor may be attached (supported) to the surface of the base particle.
- the viral infection inhibitor By attaching the viral infection inhibitor to the surface of the base particle, the viral infection inhibitor can be dispersed more uniformly in the base material. Furthermore, the surface area of the viral infection inhibitor can be increased. Therefore, sufficient contact between the viral infection inhibitor and the virus can be ensured, allowing the viral infection inhibitor to fully exert its viral infection inhibitory effect.
- the base particles to which the viral infection inhibitor is attached to the surface are not particularly limited as long as they do not inhibit the viral infection inhibitor's viral infection inhibitory effect.
- the base particles may be either resin particles or inorganic particles.
- the base particles may be used alone or in combination of two or more types.
- Synthetic resins constituting the resin particles include, for example, styrene-based resins, acrylic-based resins, urethane-based resins, vinyl chloride-based resins, ABS resins, and synthetic rubbers such as styrene-butadiene rubber (SBR) and nitrile-butadiene rubber (NBR), with styrene-based resins and acrylic-based resins being preferred.
- synthetic resin refers to a compound whose molecular main chain is mainly composed of covalent bonds and has a molecular weight of 10,000 or more.
- the molecular weight of a synthetic resin is the weight average molecular weight of the synthetic resin.
- the weight average molecular weight of a synthetic resin can be measured in the same manner as the weight average molecular weight of the above-mentioned virus infection-blocking compound.
- the styrene-based resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, styrene-based monomers such as styrene, methylstyrene, ethylstyrene, i-propylstyrene, dimethylstyrene, chlorostyrene, and bromostyrene, and copolymers containing, as monomer units, a styrene-based monomer and one or more vinyl monomers copolymerizable with the styrene-based monomer.
- styrene-based monomers such as styrene, methylstyrene, ethylstyrene, i-propylstyrene, dimethylstyrene, chlorostyrene, and bromostyrene
- the acrylic resin is not particularly limited, and examples thereof include homopolymers or copolymers containing, as monomer units, acrylic monomers such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and pentyl (meth)acrylate, and copolymers containing, as monomer units, an acrylic monomer and one or more vinyl monomers copolymerizable with the acrylic monomer.
- (meth)acrylate means acrylate or methacrylate.
- Vinyl monomers that can be copolymerized with acrylic monomers include acrylonitrile, methacrylonitrile, maleic anhydride, and acrylamide.
- the inorganic material constituting the inorganic particles is not particularly limited, and examples include zeolite, hydrotalcite, calcium carbonate, calcium citrate, magnesium carbonate, magnesium hydroxide, etc.
- the synthetic resin that constitutes the resin particles preferably contains an aromatic ring.
- the aromatic ring attracts the hydrophobic portion of the viral infection inhibiting compound attached to the surface of the resin particles and orients the secondary amino group outward, allowing the viral infection inhibiting agent to more effectively exert its viral infection inhibiting effect.
- the aromatic ring may be a monocyclic aromatic ring, or may be a combination of monocyclic aromatic rings condensed together (condensed aromatic ring).
- the aromatic ring is not particularly limited, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, biphenyl, and phenoxyphenyl.
- An aromatic ring is formed by removing (pulling out) one or more hydrogen atoms from either the aromatic ring or the condensed aromatic ring, and is bonded to another atom by a covalent bond.
- the amount of the viral infection inhibiting compound attached to the base particles is preferably 1 part by mass or more, more preferably 5 parts by mass or more, more preferably 7 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of the base particles.
- the amount of the viral infection inhibiting compound attached is 1 part by mass or more, the viral infection inhibiting agent can be uniformly attached to the surface of the base particles, and the viral infection inhibiting effect of the viral infection inhibiting agent can be more effectively exerted.
- the amount of the viral infection inhibiting compound attached to the base particle is preferably 1000 parts by mass or less, more preferably 800 parts by mass or less, more preferably 600 parts by mass or less, and even more preferably 400 parts by mass or less, per 100 parts by mass of the base particle.
- the amount of the viral infection inhibiting compound attached is 1000 parts by mass or less, the viral infection inhibiting agents do not bond to each other, and the viral infection inhibiting agent is efficiently arranged on the surface of the base particle, improving the viral infection inhibiting effect.
- the manner in which the viral infection inhibitor is attached to the surface of the base particles is not particularly limited, and may be, for example, by the adhesive strength of the viral infection inhibitor, or by using a binder resin to adhere the viral infection inhibitor to the surface of the base particles. However, since this allows the viral infection inhibitor to effectively exert its viral infection inhibitory effect, it is preferable that the viral infection inhibitor compound is attached to the surface of the base particles by the adhesive strength of the viral infection inhibitor compound itself.
- the viral infection inhibitor has a viral infection inhibitory effect against various viruses due to the action of the viral infection inhibitor compound, and exerts an excellent viral infection inhibitory effect against both enveloped and non-enveloped viruses.
- enveloped viruses examples include influenza viruses (e.g., types A and B), rubella viruses, Ebola viruses, coronaviruses (e.g., SARS virus, novel coronavirus (SARS-CoV-2)), measles viruses, chickenpox/shingles viruses, herpes simplex viruses, mumps viruses, arboviruses, respiratory syncytial viruses, hepatitis viruses (e.g., hepatitis B virus, hepatitis C virus, etc.), yellow fever viruses, AIDS viruses, rabies viruses, hantaviruses, dengue viruses, Nipah viruses, and lyssaviruses.
- influenza viruses e.g., types A and B
- rubella viruses e.g., Ebola viruses, coronaviruses (e.g., SARS virus, novel coronavirus (SARS-CoV-2)), measles viruses, chickenpox/shingles viruses, herpes simplex viruses, mumps
- Non-enveloped viruses include, for example, feline calicivirus, adenovirus, norovirus, rotavirus, human papillomavirus, poliovirus, enterovirus, coxsackievirus, human parvovirus, encephalomyocarditis virus, and rhinovirus.
- the viral infection inhibitor is used by being incorporated into a base material to which it is desired to impart a viral infection inhibitor effect, and the base material containing the viral infection inhibitor exerts a viral infection inhibitor effect as a viral infection inhibitor product.
- the substrate to be used for containing the virus infection inhibitor is not particularly limited as long as it is capable of containing the virus infection inhibitor, and examples include molded bodies such as films, paints, coatings, wallpaper, decorative sheets, flooring materials, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), interior products and interior materials for vehicles (e.g., cars, airplanes, ships, etc.) (seats, child seats, and the foams that make up these), kitchen supplies, baby products, building interior materials, etc.
- molded bodies such as films, paints, coatings, wallpaper, decorative sheets, flooring materials, textile products (woven fabrics, nonwoven fabrics, knitted fabrics), interior products and interior materials for vehicles (e.g., cars, airplanes, ships, etc.) (seats, child seats, and the foams that make up these), kitchen supplies, baby products, building interior materials, etc.
- Architectural interior materials are not particularly limited, but examples include flooring, wallpaper, ceiling materials, paint, doorknobs, switches, switch covers, wax, etc.
- In-vehicle products and materials are not particularly limited, and examples include seats, child seats, seat belts, car mats, seat covers, doors, ceiling materials, floor mats, door trim, instrument panels, consoles, glove boxes, hanging straps, handrails, etc.
- the virus infection inhibitor may be kneaded into a synthetic resin.
- a method for kneading the virus infection inhibitor into a synthetic resin involves mixing the virus infection inhibitor with the synthetic resin as a raw material to produce a resin composition, and then using this resin composition to obtain a synthetic resin molded body containing a synthetic resin and the virus infection inhibitor contained in the molded body as a virus infection prevention product by a general-purpose synthetic resin molding method.
- general-purpose synthetic resin molding methods include extrusion molding, injection molding, and blow molding.
- a resin composition containing a synthetic resin and a virus infection inhibitor may be used as a synthetic resin molding master batch, and the synthetic resin as a raw material may be mixed with the synthetic resin molding master batch to produce a synthetic resin molded body as a virus infection prevention product by a general-purpose synthetic resin molding method.
- the synthetic resin constituting the molded body is not particularly limited, and examples thereof include thermoplastic resins (e.g., polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyvinyl acetate, polyurethane, Teflon (registered trademark), acrylonitrile butadiene styrene resin, acrylonitrile styrene resin, acrylic resin, polyvinyl alcohol, polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyester, polyethylene terephthalate, polybutylene terephthalate, cyclic polyolefin, polyphenylene sulfide, polytetrafluoroethylene, polysulfone, polyethersulfone, polyarylate, polyetheretherketone, thermoplastic polyimide, polyamideimide, etc.), thermosetting resins (e.g., phenolic resin, epoxy resin, melamine resin, urea resin, unsaturated polyester resin, alkyd resin
- the content of the virus infection inhibiting compound in the resin composition (except when used as a synthetic resin molding master batch) is more preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the virus infection inhibiting compound in the resin composition (except when used as a synthetic resin molding master batch) is more preferably 10 parts by mass or less, more preferably 7 parts by mass or less, per 100 parts by mass of synthetic resin.
- the content of the virus infection inhibiting compound in the resin composition is 0.3 parts by mass or more, the virus infection inhibiting effect of the resin composition can be improved.
- the content of the virus infection inhibiting compound in the resin composition is 10 parts by mass or less, the virus infection inhibiting compound is easily dispersed uniformly without agglomeration without affecting the physical properties of the synthetic resin, thereby improving the virus infection inhibiting effect.
- the content of the viral infection inhibiting compound in the substrate is more preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more, per 100 parts by mass of the substrate.
- the content of the viral infection inhibiting compound in the substrate is more preferably 10 parts by mass or less, more preferably 7 parts by mass or less, per 100 parts by mass of the substrate.
- the content of the viral infection inhibiting compound in the substrate is 0.3 parts by mass or more, the viral infection inhibiting effect of the viral infection inhibiting product can be improved.
- the content of the viral infection inhibiting compound in the substrate is 10 parts by mass or less, the viral infection inhibiting compound is easily dispersed uniformly without agglomeration without affecting the physical properties of the substrate, improving the viral infection inhibiting effect.
- the resin composition formed by incorporating a virus infection inhibitor into a synthetic resin can be used as a masterbatch for synthetic resin molding.
- the synthetic resin used in the masterbatch for synthetic resin molding can be any of the synthetic resins exemplified as the synthetic resins that form the molded body. Only one type of synthetic resin may be used, or two or more types may be used in combination.
- the content of the virus infection-inhibiting compound in the synthetic resin molding masterbatch is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and more preferably 20 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the virus infection-inhibiting compound in the synthetic resin molding masterbatch is preferably 120 parts by mass or less, more preferably 110 parts by mass or less, more preferably 105 parts by mass or less, more preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and more preferably 60 parts by mass or less, per 100 parts by mass of synthetic resin.
- the virus infection inhibitor has excellent heat resistance, when it is added to a synthetic resin to form a resin composition, discoloration such as yellowing does not generally occur during the manufacturing process of the resulting resin composition and the synthetic resin molded article obtained by molding it, and a resin composition and synthetic resin molded article with excellent appearance can be obtained.
- the resin composition particularly the synthetic resin molding masterbatch, preferably further contains a dispersant.
- the dispersant is not particularly limited, and examples thereof include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, polyalkylene glycols (e.g., polyethylene glycol, polypropylene glycol, etc.), and the like. Polyalkylene glycols, anionic surfactants, and nonionic surfactants are preferred, and polyalkylene glycols and nonionic surfactants are more preferred.
- the interaction between the dispersant and the secondary cyclic amino structure of the virus infection inhibiting compound makes it easier to segregate (bleed out) the virus infection inhibiting compound on the surface of the resin composition and the virus infection inhibiting product (e.g., synthetic resin molded body, etc.) produced from this resin composition. Therefore, even if the virus infection inhibitor present on the surface of the resin composition and the virus infection prevention product is removed by cleaning such as wiping with water or by contact with human hands, the virus infection prevention compound can be smoothly segregated (bleed out) onto the surface of the resin composition and the virus infection prevention product, and the resin composition and the virus infection prevention product can be stably imparted with excellent virus infection prevention effects.
- the virus infection inhibiting compound e.g., synthetic resin molded body, etc.
- Anionic surfactants are not particularly limited, and examples thereof include alkyl phosphates such as sodium dodecyl phosphate, potassium dodecyl phosphate, sodium stearyl phosphate, and potassium stearyl phosphate; polyoxyethylene alkyl ether phosphate salts such as polyoxyethylene (3) lauryl ether sodium phosphate and polyoxyethylene (3) lauryl ether potassium phosphate; polyoxyethylene alkyl phenyl ether phosphate salts such as polyoxyethylene (3) lauryl phenyl ether sodium phosphate and polyoxyethylene (3) lauryl phenyl ether potassium phosphate; alkyl benzene sulfonates (e.g., sodium dodecyl benzene sulfonate, potassium dodecyl benzene sulfonate, ammonium dodecyl benzene sulfonate, and triethanol ammonium dodecyl benzene sulfonate
- Nonionic surfactants are not particularly limited, and examples thereof include polyoxyalkylene alkyl ethers (e.g., polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene polyoxypropylene lauryl ether, and other polyoxyethylene alkyl ethers, polyoxypropylene cetyl ether, polyoxypropylene isocetyl ether, polyoxypropylene stearyl ether, polyoxypropylene oleyl ether, and other polyoxypropylene alkyl ethers), polyoxyethylene alkyl phenyl ethers, polyoxyalkylene fatty acid esters (e.g., polyoxyethylene fatty acid esters such as polyethylene glycol monostearate and polyethylene glycol distearate, polyoxypropylene fatty acid esters such as polypropylene glycol monostearate and polyprop
- polyoxyethylene distyrenated phenyl ether, polyoxyalkylene alkyl ether, polyoxyalkylene fatty acid ester, fatty acid alkanolamide are preferred, polyoxyalkylene alkyl ether, polyoxyalkylene fatty acid ester, fatty acid dialkanolamide are more preferred, and polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, fatty acid diethanolamide are more preferred.
- polyoxyalkylene alkyl ethers polyoxyalkylene fatty acid esters, fatty acid dialkanolamides, glycerin fatty acid esters, and fatty alcohols are preferred, and polyoxyethylene alkyl ethers, polyoxyethylene fatty acid esters, fatty acid diethanolamides, glycerin fatty acid esters, and cetostearyl alcohol are more preferred.
- amphoteric surfactants are not particularly limited, and examples thereof include alkylaminoacetic acid betaine, alkylamidopropyl betaine, sulfobetaine, alkylamino (mono- or di-)propionate, imidazolinium betaine, alkylamine oxide, alkylaminoethyl glycine, alkyldi(aminoethyl)glycine, glycine n-(3-aminopropyl) C10-16 derivative, alkylpolyaminoethylglycine, alkyl- ⁇ -alanine, alkyldiethanolamine, polyoxyalkylene alkylamine, and oxyethylene adduct surfactants of diamine.
- the dispersant contains a polyoxyalkylene structure in the molecule.
- a polyoxyalkylene structure By containing a polyoxyalkylene structure, the interaction with the secondary cyclic amino structure of the viral infection inhibiting compound can be improved.
- a dispersant having a polyoxyalkylene structure in the molecule is more likely to segregate (bleed out) on the surface of the resin composition and the viral infection inhibiting product (e.g., a synthetic resin molded body) produced from this resin composition.
- the viral infection inhibiting compound can be further smoothly segregated (bleed out) on the surface of the resin composition and the viral infection inhibiting product, and the resin composition and the viral infection inhibiting product can be more stably imparted with an excellent viral infection inhibiting effect.
- the polyoxyalkylene structure means a repeating unit represented by the following general formula. --(R 6 --O)r-- (In the formula, R6 represents an alkylene group having 1 to 14 carbon atoms, and r represents the number of repeating units and is a natural number of 2 or more.)
- An alkylene group is a divalent atomic group resulting from the removal of two hydrogen atoms bonded to two different carbon atoms in an aliphatic saturated hydrocarbon, and includes both linear and branched atomic groups. Note that branched includes the case where one carbon (methyl group) is bonded as a side chain.
- alkylene group examples include a methylene group [ --CH2-- ], an ethylene group [ --CH2 -- CH2-- ], a propylene group [--CH( CH3 )-- CH2-- ], a trimethylene group [ --CH2 -- CH2 -- CH2-- ], a butylene group, an amylene group [--( CH2 ) 5-- ], and a hexylene group.
- the HLB value of the dispersant is preferably 10 or more, more preferably 14 or more, and even more preferably 18 or more.
- the melting point of the dispersant is preferably 40°C or higher, more preferably 45°C or higher, and more preferably 50°C or higher.
- the melting point of the dispersant is preferably 100°C or lower, more preferably 80°C or lower, and more preferably 60°C or lower. If the melting point of the dispersant is 40°C or higher, the temperature range in which the dispersant can exist as a solid is expanded, and the processability of the virus infection inhibitor is improved.
- the melting point of the dispersant is 100°C or lower, the dispersant melts when kneading the synthetic resin and the virus infection inhibitor with the dispersant, making it easier for the dispersant to come into contact with the virus infection inhibitor compound, improving the dispersibility of the virus infection inhibitor compound, and imparting an excellent virus infection inhibitory effect to the synthetic resin.
- the melting point of the dispersant refers to the temperature measured by differential scanning calorimetry in accordance with JIS K7121:1987.
- the content of the dispersant in the resin composition is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, more preferably 0.3 parts by mass or more, and more preferably 0.4 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the dispersant in the resin composition is preferably 5 parts by mass or less, more preferably 4 parts by mass or less, and more preferably 3 parts by mass or less, per 100 parts by mass of synthetic resin.
- the virus infection inhibitor When the content of the dispersant in the resin composition is 0.1 parts by mass or more, the virus infection inhibitor can be effectively segregated (bleed out) on the surface of the resin composition, and the virus infection inhibitory effect of the resin composition can be improved.
- the content of the dispersant in the resin composition is 5 parts by mass or less, the virus infection inhibitor compound can be easily dispersed uniformly without agglomeration without affecting the physical properties of the substrate, thereby improving the virus infection inhibitory effect of the virus infection inhibitor product.
- the content of the dispersant in the substrate is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, more preferably 0.3 parts by mass or more, and more preferably 0.4 parts by mass or more, per 100 parts by mass of the substrate.
- the content of the dispersant in the substrate is preferably 5 parts by mass or less, more preferably 4 parts by mass or less, and more preferably 3 parts by mass or less, per 100 parts by mass of the substrate.
- the virus infection inhibitory compound can be easily dispersed uniformly without agglomeration without affecting the physical properties of the substrate, thereby improving the virus infection inhibitory effect of the virus infection inhibitory product.
- the content of the dispersant in the synthetic resin molding masterbatch is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and more preferably 8 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the dispersant in the synthetic resin molding masterbatch is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and more preferably 20 parts by mass or less, per 100 parts by mass of synthetic resin.
- the virus infection inhibitor has excellent heat resistance. Therefore, even when a resin composition containing the virus infection inhibitor and a synthetic resin molded body obtained by molding the same are used in a high-temperature environment, the occurrence of yellowing in the resin composition and the synthetic resin molded body can be largely suppressed. Furthermore, by adding an antioxidant to the resin composition, particularly the synthetic resin molding masterbatch, the above-mentioned yellowing can be more effectively suppressed.
- the antioxidant is not particularly limited, and examples thereof include phosphorus-based antioxidants, phenol-based antioxidants, and thioether-based antioxidants.
- the synthetic resin contains a viral infection inhibitor
- the viral infection inhibitor and the antioxidant can be well dispersed in the synthetic resin without affecting the viral infection inhibitor's viral infection inhibitory effect. Therefore, phosphorus-based antioxidants and thioether-based antioxidants are preferred, phosphorus-based antioxidants and dialkylthiodipropionates are more preferred, and phosphorus-based antioxidants are more preferred.
- the resin composition further contains an antioxidant, particularly a phosphorus-based antioxidant or a thioether-based antioxidant, the heat resistance of the resulting resin composition and viral infection inhibitor product is further improved, and a viral infection inhibitor product with excellent appearance can be obtained for a long period of time.
- an antioxidant particularly a phosphorus-based antioxidant or a thioether-based antioxidant
- the phosphorus-based antioxidant is not particularly limited, and examples thereof include tridecyl phosphite, tris(tridecyl)phosphite, tristearyl phosphite, triphenyl phosphite, trinonylphenyl phosphite, bis(tridecyl)pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, bis(decyl)pentaerythritol diphosphite, tris(2,4-di-t-butylphenyl)phosphite, bis(2,4-di-t-butyl-6-methylphenyl)ethyl.
- phosphates examples include ester phosphorous acid, 2,2'-methylenebis(4,6-di-t-butyl-1-phenyloxy)(2-ethylhexyloxy)phosphorus, 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexylphosphite, diethyl(3,5-di-t-butyl-4-hydroxybenzyl)phosphonate, and stearyl acid phosphate zinc salt, with distearyl pentaerythritol diphosphite and tris(2,4-di-t-butylphenyl)phosphite being preferred.
- Phenol-based antioxidants are not particularly limited, and examples thereof include 2,6-di-t-butyl-p-cresol (BHT), butyl hydroxyanisole (BHA), 2,6-di-t-butyl-4-ethylphenol, stearyl- ⁇ -(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2'-methylene bis-(4-methyl-6-butylphenol), 2,2'-methylene bis-(4-ethyl-6-t-butylphenol), 4,4'-butylidene-bis-(3-methyl-6-t-butylphenol), 1,1,3-tris-(2-methyl-hydrogen bis(3,3'-t-butylphenol) butane, tetrakis[methylene-3-(3',5'-butyl-4-hydroxyphenyl)propionate]methane, 1,3,3-tris-(2-methyl-4-hydroxy-5-t-butylphenol) but
- Thioether-based antioxidants are not particularly limited, and examples thereof include dialkyl thiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetra( ⁇ -alkylthiopropionic acid) esters, with dialkyl thiodipropionates being preferred, and dilauryl thiodipropionate being more preferred.
- dialkyl thiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate
- pentaerythritol tetra( ⁇ -alkylthiopropionic acid) esters with dialkyl thiodipropionates being preferred, and dilauryl thiodipropionat
- the content of the antioxidant in the resin composition is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, more preferably 0.03 parts by mass or more, and more preferably 0.05 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the antioxidant in the resin composition is preferably 0.5 parts by mass or less, more preferably 0.4 parts by mass or less, and more preferably 0.3 parts by mass or less, per 100 parts by mass of synthetic resin.
- the content of the antioxidant in the synthetic resin molding masterbatch is preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, and more preferably 0.8 parts by mass or more, per 100 parts by mass of synthetic resin.
- the content of the antioxidant in the synthetic resin molding masterbatch is preferably 4 parts by mass or less, more preferably 3 parts by mass or less, and more preferably 2 parts by mass or less, per 100 parts by mass of synthetic resin.
- the synthetic resin molding masterbatch is preferably in the form of resin pellets, as they have excellent moldability.
- a virus infection prevention product synthetic resin molded body
- excellent virus infection prevention effects can be obtained.
- the shape of the resin pellets is not particularly limited, and examples include spherical, cylindrical, and prismatic shapes. From the viewpoint of pellet shape stability, a cylindrical shape is preferred.
- the maximum length dimension of the resin pellets is preferably 1 mm or more, and more preferably 3 mm or more.
- the maximum length dimension of the resin pellets is preferably 10 mm or less, and more preferably 7 mm or less.
- the synthetic resin molding master batch can be used by mixing with other resin materials.
- the other resin materials may be resin pellets.
- the synthetic resin molding master batch and the other resin materials are mixed to obtain a mixed resin material, which is then molded to obtain a virus infection prevention product (synthetic resin molded body) with excellent virus infection prevention effects.
- a virus infection inhibitor paint By incorporating a virus infection inhibitor into paint, a virus infection inhibitor paint can be produced.
- the virus infection inhibitor has excellent dispersibility in paint, so the coating film formed from the virus infection inhibitor paint has excellent virus infection inhibition effects as a virus infection inhibitor product.
- a conventionally known paint is used as the paint.
- Either hydrophobic paint or hydrophilic paint can be used as the paint.
- the paint include oil-based paint (e.g., mixed paint, oil varnish, etc.), cellulose paint, and synthetic resin paint.
- the paint also includes photocurable paint that polymerizes when exposed to radiation such as ultraviolet light to produce a binder component.
- the hydrophilic paint examples of the paint include water-based urethane paint, water-based silicone paint, water-based fluorine paint, and water-based inorganic paint.
- the paint may contain additives such as pigments, plasticizers, hardeners, extenders, fillers, antioxidants, and thickeners, as long as the additives do not impair the paint's physical properties.
- Methods for incorporating a virus infection inhibitor in paint include, for example, supplying the virus infection inhibitor and paint to a dispersing device and mixing them uniformly. Examples of dispersing devices include high-speed mills, ball mills, and sand mills.
- the paint may contain a solvent to adjust the viscosity.
- a solvent an organic solvent is preferable because it improves the dispersibility of the virus infection inhibitor in the paint.
- the organic solvent is not particularly limited, and examples thereof include toluene, xylene, methyl ethyl ketone, acetone, ethyl acetate, benzene, and isopropyl alcohol.
- the solvent may be used alone or in combination of two or more kinds.
- the content of the virus infection inhibiting compound in the virus infection inhibiting paint is preferably 1% by mass or more, and more preferably 2% by mass or more.
- the content of the virus infection inhibiting compound in the virus infection inhibiting paint is preferably 10% by mass or less, more preferably 7% by mass or less, and more preferably 5% by mass or less.
- the coating film formed from the virus infection inhibiting paint exhibits excellent virus infection inhibiting effect.
- the content of the virus infection inhibiting compound is 10% by mass or less, the virus infection inhibiting compound does not aggregate and is easily dispersed uniformly, improving the virus infection inhibiting effect.
- the initial yellowing resistance of the virus infection prevention product is preferably 15 or less, more preferably 13 or less, and more preferably 12 or less.
- the durable yellowing resistance of the virus infection prevention product is preferably 25 or less, more preferably 24 or less, more preferably 23 or less, and more preferably 22 or less.
- yellowing b*1 is measured using a spectrophotometer.
- a blank virus infection-inhibiting product is prepared in the same manner except that no virus infection inhibitor is added, and yellowing b*2 is measured.
- Durable yellowing resistance is measured by leaving the virus infection prevention product in an oven set at 120°C for 120 hours, and then calculating the yellowing ⁇ b* in the same manner as for the initial yellowing resistance described above.
- Virus infection-inhibiting compounds 1-10, dispersants 1-9, and antioxidants 1-8 were prepared.
- Viral infection-blocking compound 1 [formula (2), manufactured by ADEKA Corporation, trade name "ADEKA STAB LA-77Y"]
- Viral infection blocking compound 2 [PHMB (polyhexamethylene biguanide)] Polyhexamethylene biguanide does not have a secondary cyclic amino structure.
- Viral infection-inhibiting compound 3 [formula (4)] A viral infection-inhibiting compound commercially available from Nittobo Medical Co., Ltd. under the product name "PAA-15C" was freeze-dried to obtain a powder of viral infection-inhibiting compound 3.
- m is the number of repeating units and is a natural number of 2 or more.
- Viral infection-inhibiting compound 5 [Formula (6), product name "ADEKA STAB LA-402AF” manufactured by ADEKA Corporation, in formula (6), R 1 is an alkyl group.]
- *1 and *4 to *8 are bonds and mean single bonds.
- Bond *8 is bonded to any of bonds *4 to *7 of B.T.C.
- R3 is bonded to any of bonds *4 to *7 of B.T.C. except for the bond bonded to bond *8.
- p is the number of repeating units and is a natural number of 2 or more.
- *10 to *15 are bonds and represent single bonds.
- Bond *14 is bonded to any of bonds *10 to *13 of B.T.C.
- R5 is bonded to any of bonds *10 to *13 of B.T.C. except for the bond bonded to bond *14.
- q is the number of repeating units and is a natural number of 2 or more.
- Dispersant 1 polyethylene glycol distearate, HLB value: 18.9, melting point: 56°C Dispersant 2: Polyethylene glycol monostearate, HLB value: 19.4, melting point: 59°C Dispersant 3: Polyethylene glycol, HLB value: 20, melting point: 57.5°C, molecular weight: 3100 Dispersant 4: Polyoxyethylene lauryl ether, HLB value: 9.7, melting point: 16°C Dispersant 5: Lauric acid diethanolamide, HLB value: 5.8, melting point: 40°C Dispersant 6: Glycerol fatty acid ester, HLB value: 2.8, melting point: 56 to 60°C Dispersant 7: Cetostearyl alcohol, HLB value: 1.3, melting point: 51-54°C Dispersant 8: Polyethylene glycol, HLB value: 20, melting point: 60°C, molecular weight: 8800 Dispersant 9: Polyethylene glycol, HLB value: 20, melting point: 58°C, molecular weight: 1
- Antioxidant 1 Distearyl pentaerythritol diphosphite (manufactured by Johoku Chemical Industry Co., Ltd., product name "JPP-2000PT”)
- Antioxidant 2 Antioxidant 1 and tris(2,4-di-t-butylphenyl)phosphite (manufactured by BASF Japan, product name "Irgafos 168") mixed in a mass ratio of 1:1.
- Antioxidant 3 Dilauryl thiodipropionate (manufactured by Ouchi Shinko Chemical Industry, product name "Nocrac 400”)
- Antioxidant 4 2,2'-methylenebis(4,6-di-t-butylphenyl)2-ethylhexyl phosphite (manufactured by ADEKA Corporation, product name "ADEKA STAB HP-10")
- Antioxidant 5 Tristearyl phosphite (manufactured by Johoku Chemical Industry Co., Ltd., product name "JP-318E”)
- Antioxidant 6 Diethyl (3,5-di-t-butyl-4-hydroxybenzyl)phosphonate (manufactured by Johoku Chemical Industry Co., Ltd., product name "JC-356”)
- Antioxidant 7 Stearyl acid phosphate zinc salt (manufactured by Johoku Chemical Industry Co., Ltd., product name "JP-518Zn”)
- Antioxidant 8
- the viral infection-inhibiting compound was coarsely ground using a roll press device (Seishin Enterprise Co., Ltd., product name "150 type”) at an operating condition of a rotation speed of 25 rpm and a pressing force of 25 tons, and then ground using a jet mill device (Nisshin Engineering Co., Ltd., product name "SJ-500”) under operating conditions of a viral infection-inhibiting compound supply rate of 1 kg/h and a compressed air pressure of 0.75 MPa to obtain particles of the viral infection-inhibiting compound.
- a roll press device Seishin Enterprise Co., Ltd., product name "150 type
- a jet mill device Neshin Engineering Co., Ltd., product name "SJ-500
- Examples 1, 3 to 19 and Comparative Examples 1 to 9 Particles of the virus infection inhibiting compound of the type shown in Table 1 were prepared as a virus infection inhibiting agent.
- a masterbatch for synthetic resin molding was prepared by melt-kneading and mixing the particles of the virus infection inhibiting compound, polypropylene, and the dispersant and antioxidant of the type shown in Table 1 in the mass ratio (mass %) of the masterbatch shown in Table 1. The amount (mass %) of each component is shown in the "Mass ratio of masterbatch" column in Table 1 as "mass of virus infection inhibiting compound/mass of polypropylene/mass of dispersant/mass of antioxidant".
- the obtained synthetic resin molding master batch and separately prepared polypropylene (manufactured by Japan Polypropylene, product name "Novatec PP BC6C") were mixed with the virus infection inhibiting compound, polypropylene, and the type of dispersant and antioxidant shown in Table 1 so as to obtain the mass ratio (mass %) of the resin composition shown in Table 1, and the mixture was melt-kneaded at 180°C for 5 minutes to prepare a resin composition.
- the amount (mass %) of each component is shown in the "mass ratio of resin composition” column in Table 1 as "mass of virus infection inhibiting compound/mass of polypropylene/mass of dispersant/antioxidant".
- the resulting resin composition was press molded to obtain a sheet-shaped synthetic resin molded body with an average thickness of 1 mm as a viral infection prevention product.
- Example 2 Particles of the viral infection inhibiting compound of the type shown in Table 1 were prepared as a viral infection inhibiting agent.
- a viral infection inhibiting paint was prepared by mixing a viral infection inhibiting agent containing 5 parts by mass of the viral infection inhibiting compound with 95 parts by mass of an ultraviolet-curing acrylic paint (UV-curing resin, manufactured by Coattec Co., Ltd., product name "AI-N2").
- UV-curing resin manufactured by Coattec Co., Ltd., product name "AI-N2”
- the viral infection inhibiting paint was applied to a polyethylene film using a wire bar coater #8 to a thickness of 18 ⁇ m to form a coating layer.
- the coating layer was irradiated with ultraviolet light having a wavelength of 365 nm at 25°C to an integrated light dose of 500 mJ/ cm2 , curing the ultraviolet-curing acrylic paint and obtaining a coating film with a thickness of 18 ⁇ m as a virus infection prevention product.
- the dispersibility and yellowing resistance of the obtained virus infection prevention product were measured as follows, and the results are shown in Table 2.
- the antiviral activity of the resulting viral infection-blocking product was measured as described below, and the results are shown in Table 2.
- a square planar measurement area with sides of 50 mm was determined on any part of the surface of the obtained virus infection-inhibiting product, and the presence or absence of aggregates of the virus infection-inhibiting compound in this measurement area was visually confirmed. Dispersibility was evaluated based on the following criteria. A: No aggregates were present. B: Aggregates were present.
- the obtained virus infection-inhibiting product was measured for yellowing b*1 using a spectrophotometer (manufactured by Konica Minolta, Inc., product name "CM-5").
- a blank virus infection-inhibiting product was prepared in the same manner as above, except that no virus infection inhibitor was added, and yellowing b*2 was measured.
- the viral infection-inhibiting products obtained above were subjected to antiviral tests using feline calicivirus (non-enveloped virus) and influenza virus (enveloped virus) in the following manner.
- test specimens were prepared by cutting out a flat square shape with each side measuring 5.0 cm.
- the surface of the obtained test piece was wiped with a flat square nonwoven fabric measuring 10 cm on a side (manufactured by Nippon Paper Crecia Co., Ltd., product name "Kimwipe S-200") by moving it back and forth 10 times to prepare a test specimen.
- test time 24 hours
- test time 24 hours
- virus infectivity common logarithm value
- a blank reference specimen was prepared in the same manner as above, except that no viral infection inhibitor was added, and the viral infectivity titer (common logarithm value) (PFU/ cm2 ) was calculated based on this blank reference specimen in the same manner as above.
- the viral infectivity titer (common logarithm value) of the blank reference specimen was 6.5 PFU/ cm2 .
- the antiviral activity value was calculated by subtracting the viral infectivity of the test specimen from the viral infectivity of the blank reference specimen.
- the viral infection inhibitor of the present invention has a viral infection inhibitory effect against various viruses due to the action of the viral infection inhibitor compound.
- the viral infection inhibitor can be imparted with a viral infection inhibitory effect by being contained in various base materials.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2022025137A1 (ja) * | 2020-07-30 | 2022-02-03 | 大日本印刷株式会社 | 抗ウイルス性物品及び抗ウイルス性樹脂組成物 |
| JP2022057868A (ja) * | 2020-09-30 | 2022-04-11 | イビデン株式会社 | 抗ウィルス基体 |
| WO2023026955A1 (ja) * | 2021-08-27 | 2023-03-02 | 積水化学工業株式会社 | 抗ウイルス性部材 |
| JP2023147179A (ja) * | 2022-03-29 | 2023-10-12 | 大日精化工業株式会社 | 抗ウイルス剤、抗ウイルス性樹脂組成物、及び抗ウイルス性物品 |
-
2024
- 2024-04-18 JP JP2024527185A patent/JPWO2024219467A1/ja active Pending
- 2024-04-18 WO PCT/JP2024/015429 patent/WO2024219467A1/ja not_active Ceased
- 2024-04-19 TW TW113114626A patent/TW202448449A/zh unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022025137A1 (ja) * | 2020-07-30 | 2022-02-03 | 大日本印刷株式会社 | 抗ウイルス性物品及び抗ウイルス性樹脂組成物 |
| JP2022057868A (ja) * | 2020-09-30 | 2022-04-11 | イビデン株式会社 | 抗ウィルス基体 |
| WO2023026955A1 (ja) * | 2021-08-27 | 2023-03-02 | 積水化学工業株式会社 | 抗ウイルス性部材 |
| JP2023147179A (ja) * | 2022-03-29 | 2023-10-12 | 大日精化工業株式会社 | 抗ウイルス剤、抗ウイルス性樹脂組成物、及び抗ウイルス性物品 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2024219467A1 (https=) | 2024-10-24 |
| TW202448449A (zh) | 2024-12-16 |
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